Middlesboro, KY Homes

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  /18

  $70,000

  $55K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,426 Sq Ft

  123 Cawood Ln, Middlesboro, KY 40965

  Major Price Reduction!!Charming 2 bedroom, 1.5 bath home situated on a beautiful, quiet lot with plenty of potential and possibilities! This property features an extra-large carport, storage shed, and inviting front porch perfect for enjoying peaceful mornings or evenings outdoors. The large backyard offers plenty of space for entertaining, gardening, or relaxing, while the enclosed back

  

  Dustin Daniels

  Mountain Realty

  123 Cawood Ln, Middlesboro, KY 40965
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  /2

  $1,200 Per Month

  • 2 Beds
  • 1 Bath
  • 680 Sq Ft
  • Townhouse for Rent

  912 Rochester Ave, Middlesboro, KY 40965

  Property Id: 2768909 Welcome to your new home in Middlesboro, KY! This charming 2 bedroom, 1 bathroom townhouse is perfect for a small family or roommates. Built in 1995, this cozy property features a spacious kitchen with oven and refrigerator, central heat and air, laminate flooring, washer/dryer hookups, and a beautiful lawn. Enjoy the convenience of a private driveway and the company of

  912 Rochester Ave, Middlesboro, KY 40965
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  /11

  $152,500

  Sold Oct 10, 2025

  102 Stone Creek Dr, Middlesboro, KY 40965

  • 2 Beds
  • 1 Bath
  • 952 Sq Ft
  • Built 2000

  Last Sold Summary

  • 10% Below List Price
  • $160/SF
  • 9 Days On Market

  Current Estimated Value $151,207

  Last Listing Agent Misti McGrath Realty Group

  102 Stone Creek Dr, Middlesboro, KY 40965
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  /8

  Est $68,942

  Not Listed For Sale

  108 S 8th St, Middlesboro, KY 40965

  • 2 Beds
  • 1 Bath
  • 700 Sq Ft
  • Built 1935

  108 S 8th St, Middlesboro, KY 40965

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Jason Szaks EXIT Town & Country Realtors
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  /20

  $369,000

  $30K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 3,397 Sq Ft

  103 Kingsbury Woods Rd, Middlesboro, KY 40965

  Rare opportunity to own a premier golf course property on Hole #2 at the Middlesboro Golf Course—one of only four homes situated directly on the course. Perfectly positioned on a generous 0.67-acre lot, this spacious residence offers a grand total living space, including a finished basement, providing plenty of room to live, entertain, and relax. With three bedrooms and three full baths, the home

  Anthony Gigilo ListWithFreedom.com

  103 Kingsbury Woods Rd, Middlesboro, KY 40965
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  /11

  $1,200 Per Month

  • 2 Beds
  • 1 Bath
  • 700 Sq Ft
  • Condo for Rent

  1027 Chichester Ave Unit B, Middlesboro, KY 40965

  Property Id: 2575456 Available Now! Included: • 2 Bedrooms / 1 Bathroom • Pet-Friendly (on approval) • Washer & Dryer • Large Yard - Lawn care included! • Quiet cul-de-sac Tenant Pays: • Electricity • Water & Garbage • Virtual Tour 1st months rent, security is the same as rent amount. Non-refundable

  1027 Chichester Ave Unit B, Middlesboro, KY 40965
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  /2

  $170,000

  Sold Jun 04, 2026

  4605 W Cumberland Ave, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,056 Sq Ft
  • Built 1995

  Last Sold Summary

  • 3% Above List Price
  • $161/SF
  • 37 Days On Market

  Current Estimated Value $157,031

  Last Listing Agent Virginia Wilder Century 21 Virginia Wilder Real Estate

  4605 W Cumberland Ave, Middlesboro, KY 40965
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  /13

  Est $155,348

  Not Listed For Sale

  514 Avondale Ave, Middlesboro, KY 40965

  • 4 Beds
  • 3 Baths
  • 2,627 Sq Ft
  • Built 1985

  514 Avondale Ave, Middlesboro, KY 40965

  Last Sold Summary

  • 34 Days On Market

  Last Listing Agent Misti McGrath Realty Group
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  /11

  $35,000

  $15K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 728 Sq Ft

  105 Nutwood Rd, Middlesboro, KY 40965

  3 bed, 1 bath fixer-upper in Middlesboro, KY! Great investment opportunity—flip, rent, or make it your own. City water/sewer (per public record). Priced for potential—bring your ideas!

  Megan Stanaford Black Diamond Realty

  105 Nutwood Rd, Middlesboro, KY 40965
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  /11

  $1,200 Per Month

  • 2 Beds
  • 1 Bath
  • 700 Sq Ft
  • Condo for Rent

  1027 Chichester Ave Unit B, Middlesboro, KY 40965

  Property Id: 2575456 Available Now! Included: • 2 Bedrooms / 1 Bathroom • Pet-Friendly (on approval) • Washer & Dryer • Large Yard - Lawn care included! • Quiet cul-de-sac Tenant Pays: • Electricity • Water & Garbage • Virtual Tour 1st months rent, security is the same as rent amount. Non-refundable

  1027 Chichester Ave Unit B, Middlesboro, KY 40965
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  /30

  $202,000

  Sold Feb 17, 2026

  140 Chasteen Dr, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft
  • Built 1954

  Last Sold Summary

  • 6% Below List Price
  • $112/SF
  • 4 Days On Market

  Current Estimated Value $223,320

  Last Listing Agent Kevin Bisceglia Coldwell Banker Bisceglia Realty & Auction Co

  140 Chasteen Dr, Middlesboro, KY 40965
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  /20

  Est $164,018

  Not Listed For Sale

  316 Avondale Ave, Middlesboro, KY 40965

  • 3 Beds
  • 1 Bath
  • 1,456 Sq Ft
  • Built 1997

  316 Avondale Ave, Middlesboro, KY 40965

  Last Sold Summary

  • 55 Days On Market

  Last Listing Agent Sharon Teaney Century 21 Virginia Wilder Real Estate
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  /28

  $39,900

  $20K PRICE DROP

  • Land
  • 4.24 Acres
  • $9,410 per Acre

  1197 Beans Fork Rd, Middlesboro, KY 40965

  Opportunity awaits on this 4.24-acre tract offering a peaceful setting with endless potential. The property was previously improved with a home that has recently been lost to fire, presenting a unique chance to start fresh and bring your vision to life. With utilities previously in place (buyer to verify), this parcel may offer a head start for rebuilding, whether you're considering a custom

  SARAH RICHARDS RE/MAX Preferred Group

  1197 Beans Fork Rd, Middlesboro, KY 40965
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  /19

  $1,600 Per Month

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft
  • House for Rent

  715 Gloucester Ave, Middlesboro, KY 40965

  Located in Middlesboro KY you will find this 3 bedroom 2 bath, brick ranch style home with an attached 1 car garage. Very spacious living room with large kitchen with lots of cabinetry and countertop space including a kitchen island. Owner's suite includes a large closet and ensuite bathroom which includes a walk-in shower and a tub! This home is located approximately 10-15 minutes from the main

  Nichole Goins Heartland Real Estate, LLC

  715 Gloucester Ave, Middlesboro, KY 40965
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  /30

  $65,000

  Sold Jul 31, 2026

  316 Exeter Ave, Middlesboro, KY 40965

  • 4 Beds
  • 2 Baths
  • 2,592 Sq Ft
  • Built 1920

  Last Sold Summary

  • 48% Below List Price
  • $25/SF
  • 12 Days On Market

  Current Estimated Value $122,250

  Last Listing Agent Steve Mason REMAX PROFESSIONAL'S

  316 Exeter Ave, Middlesboro, KY 40965
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  /28

  Est $94,304

  Not Listed For Sale

  333 Avondale Ave, Middlesboro, KY 40965

  • 3 Beds
  • 1 Bath
  • 770 Sq Ft
  • Built 1930

  333 Avondale Ave, Middlesboro, KY 40965

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent Beth Combs Turn Key Realty
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  /5

  $855,000

  • 2 Beds
  • 2 Baths
  • 15,119 Sq Ft

  725 19th St, Middlesboro, KY 40965

  Prime Multifamily Investment Opportunity Presenting a well-established commercial apartment building in the heart of Middlesboro, Kentucky. Built in 1990, this single-story property offers approximately 15,225 square feet of space ideally suited for residential rental units, providing stable cash flow in a convenient location. Strategically positioned on N 19th Street, the building benefits from

  Beth Combs Backwoods Realty & Development

  725 19th St, Middlesboro, KY 40965
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  /15

  $105,000

  Sold Apr 17, 2026

  921 Winchester Ave, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft
  • Built 1940

  Last Sold Summary

  • 9% Below List Price
  • $78/SF
  • 98 Days On Market

  Current Estimated Value $113,326

  Last Listing Agent Virginia Wilder Century 21 Virginia Wilder Real Estate

  921 Winchester Ave, Middlesboro, KY 40965
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  /42

  Est $128,837

  Not Listed For Sale

  215 Armadale Ave, Middlesboro, KY 40965

  • 3 Beds
  • 1 Bath
  • 1,120 Sq Ft
  • Built 1985

  215 Armadale Ave, Middlesboro, KY 40965

  Last Sold Summary

  • 40 Days On Market

  Last Listing Agent Beth Combs Turn Key Realty
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  /16

  $60,000

  • 3 Beds
  • 1 Bath
  • 768 Sq Ft

  712 Balmoral Rd, Middlesboro, KY 40965

  Investment opportunity with this 3 bedroom 1 bathroom home. Owner is relocating for work and must sell. The home is in progress of being renovated. Call for more info.

  Megan Stanaford Black Diamond Realty

  712 Balmoral Rd, Middlesboro, KY 40965
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  /2

  $167,000

  Sold Sep 15, 2025

  414 SE North 24th St, Middlesboro, KY 40965

  • 4 Beds
  • 2 Baths
  • 1,600 Sq Ft
  • Built 1972

  Last Sold Summary

  • 10% Below List Price
  • $104/SF
  • 2 Days On Market

  Current Estimated Value $176,930

  Last Listing Agent Beth Combs Turn Key Realty

  414 SE North 24th St, Middlesboro, KY 40965
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  /45

  Est $349,790

  Not Listed For Sale

  915 E Lothbury Ave, Middlesboro, KY 40965

  • 3 Beds
  • 4 Baths
  • 2,349 Sq Ft
  • Built 1945

  915 E Lothbury Ave, Middlesboro, KY 40965

  Last Sold Summary

  • 23 Days On Market

  Last Listing Agent Russell Tribell Fathom Realty East TN
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  /5

  $30,000

  • Land
  • 1.26 Acres
  • $23,810 per Acre

  0 Lots 12 & 13 Sams Mountain Rd Unit 1328410, Middlesboro, KY 40965

  LOCATION!! LOCATION!! Ready to build your dream home. Property is located minutes from Middlesboro. Wooded lot with electric and water available. Close to shopping, restaurants and hospitals. Minutes from LMU main campus. Buyer to verify acres!

  Sharon Teaney Century 21 Virginia Wilder Real Estate

  0 Lots 12 & 13 Sams Mountain Rd Unit 1328410, Middlesboro, KY 40965
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  /2

  $10,000

  Sold Oct 17, 2025

  Lot #1 Bellwood Rd, Middlesboro, KY 40965

  • Land
  • 12,196 Sq Ft
  • $35,714 per Acre

  Last Sold Summary

  • 50% Below List Price
  • 42 Days On Market

  Last Listing Agent Sheila Durham Coldwell Banker Bisceglia Realty & Auction Co

  Lot #1 Bellwood Rd, Middlesboro, KY 40965
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  /19

  Est $177,453

  Not Listed For Sale

  225 N 10th St, Middlesboro, KY 40965

  • 3 Beds
  • 1.5 Baths
  • 1,014 Sq Ft
  • Built 1930

  225 N 10th St, Middlesboro, KY 40965

  Last Sold Summary

  • 90 Days On Market

  Last Listing Agent Misti McGrath Realty Group
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  /2

  $50,000

  • Land
  • 16,639 Sq Ft
  • $130,890 per Acre

  0000 Edgewood Rd, Middlesboro, KY 40965

  Lot on Edgewood road, can be purchased with 205 N 20th Street Middlesboro KY; former duplex was removed and now vacant land. City utilities available.

  Megan Stanaford Black Diamond Realty

  0000 Edgewood Rd, Middlesboro, KY 40965
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  /24

  $196,000

  Sold Nov 26, 2025

  515 N 25th St, Middlesboro, KY 40965

  • 3 Beds
  • 1 Bath
  • 2,000 Sq Ft
  • Built 1918

  Last Sold Summary

  • 2% Below List Price
  • $98/SF
  • 117 Days On Market

  Current Estimated Value $191,812

  Last Listing Agent Misti McGrath Realty Group

  515 N 25th St, Middlesboro, KY 40965
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  /34

  Est $229,381

  Not Listed For Sale

  215 S 15th St, Middlesboro, KY 40965

  • 4 Beds
  • 2.5 Baths
  • 1,824 Sq Ft
  • Built 1980

  215 S 15th St, Middlesboro, KY 40965

  Last Sold Summary

  • 35 Days On Market

  Last Listing Agent Beth Combs Turn Key Realty
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  /18

  $110,000

  $25K PRICE DROP Pre-Foreclosure

  • 3 Beds
  • 1.5 Baths
  • 1,963 Sq Ft

  901 Exeter Ave, Middlesboro, KY 40965

  Hey Neighbors! If you've been looking for a solid property with room to build some serious sweat equity, you'll want to take a look at this one. Sitting on a spacious corner lot inside the Middlesboro city limits, this 1.5-story brick veneer home offers a massive 1,963 square feet of living space and sits on over half an acre 0.539 acres per (Bell County PVA). With a potential of 4 bedrooms, 2

  Russell Tribell Fathom Realty KY LLC

  901 Exeter Ave, Middlesboro, KY 40965
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  /2

  $13,000

  Sold Sep 25, 2025

  Lot #6 Bellwood Rd, Middlesboro, KY 40965

  • Land
  • 17,859 Sq Ft
  • $31,707 per Acre

  Last Sold Summary

  • 35% Below List Price
  • 14 Days On Market

  Last Listing Agent Sheila Durham Coldwell Banker Bisceglia Realty & Auction Co

  Lot #6 Bellwood Rd, Middlesboro, KY 40965
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  /17

  Est $144,975

  Not Listed For Sale

  524 E Lothbury Ave, Middlesboro, KY 40965

  • 2 Beds
  • 1 Bath
  • 800 Sq Ft
  • Built 2018

  524 E Lothbury Ave, Middlesboro, KY 40965

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Michael Hensley REMAX PROFESSIONAL'S
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  /17

  $129,900

  $30K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,908 Sq Ft

  405 S 37th St, Middlesboro, KY 40965

  Looking for a home to raise your family? Don't let this one go by! Spacious 4 bedrooms, 2 bath home with a fenced in yard, this one is just the right size for a growing family. Just minutes from the hospital and schools, yet tucked away on a side street with little traffic. Let us show you your new home today! Schedule a showing before it's gone.

  Kevin Bisceglia Coldwell Banker Bisceglia Real

  405 S 37th St, Middlesboro, KY 40965
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  /18

  $95,000

  Sold May 22, 2026

  1009 E Cumberland Ave, Middlesboro, KY 40965

  • 2 Beds
  • 1 Bath
  • 850 Sq Ft
  • Built 1935

  Last Sold Summary

  • 17% Below List Price
  • $112/SF
  • 12 Days On Market

  Current Estimated Value $97,896

  Last Listing Agent Michael Hensley REMAX PROFESSIONAL'S

  1009 E Cumberland Ave, Middlesboro, KY 40965
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  /11

  Est $184,561

  Not Listed For Sale

  403 E Lothbury Ave, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 3,360 Sq Ft
  • Built 1972

  403 E Lothbury Ave, Middlesboro, KY 40965

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent Linda Pope Renaissance Realty Group
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  /46

  $315,000

  $10K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,488 Sq Ft

  1015 Old Wilson Ln, Middlesboro, KY 40965

  Super nice four bedroom, two and 1/2 bath, 2488 sq ft with hardwood floors on a level lot in Middlesboro. Welcome to a home designed for the way you live. This stunning split level residence offers the perfect architectural solution for those seeking distinct spaces without sacrificing an open feel. This home offers privacy and distinct zones for living, working and relaxing. Great location

  David Gambrell Coldwell Banker Bisceglia Realty & Auction Co

  1015 Old Wilson Ln, Middlesboro, KY 40965
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  /20

  $240,000

  Sold Jan 30, 2026

  220 Windermere Dr, Middlesboro, KY 40965

  • 3 Beds
  • 2.5 Baths
  • 1,692 Sq Ft
  • Built 2003

  Last Sold Summary

  • 11% Below List Price
  • $142/SF
  • 108 Days On Market

  Current Estimated Value $273,207

  Last Listing Agent Sheila Durham Coldwell Banker Bisceglia Realty & Auction Co

  220 Windermere Dr, Middlesboro, KY 40965
• 

  

  /18

  Est $125,609

  Not Listed For Sale

  508 Wilderness Rd, Middlesboro, KY 40965

  • 3 Beds
  • 1 Bath
  • 1,320 Sq Ft
  • Built 1900

  508 Wilderness Rd, Middlesboro, KY 40965

  Last Sold Summary

  • 19 Days On Market

  Last Listing Agent Brad Cawood Turn Key Realty
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  /26

  $199,900

  $20K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,612 Sq Ft

  140 Wellington Dr, Middlesboro, KY 40965

  Nice 3-bedroom 2 bath home just for the picking. Priced is right with the possibility of a 4th bedroom. The kitchen, dining room, living room, 3 bedrooms and 1 bath are on the main level. The bonus room (optional 4th bedroom), full bath with laundry facilities downstairs. This home has a back deck, patio and storage building. Don't let this one get away!

  Janice Pratt Fathom Realty TN LLC

  140 Wellington Dr, Middlesboro, KY 40965
• 

  

  /27

  $164,000

  Sold Feb 21, 2026

  103 Leafwood Rd, Middlesboro, KY 40965

  • 2 Beds
  • 2 Baths
  • 1,326 Sq Ft
  • Built 1923

  Last Sold Summary

  • 1% Below List Price
  • $124/SF
  • 4 Days On Market

  Current Estimated Value $168,891

  Last Listing Agent Michael Hensley REMAX PROFESSIONAL'S

  103 Leafwood Rd, Middlesboro, KY 40965
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  /25

  Est $146,567

  Not Listed For Sale

  422 Wilderness Rd, Middlesboro, KY 40965

  • 2 Beds
  • 1 Bath
  • 850 Sq Ft

  422 Wilderness Rd, Middlesboro, KY 40965

  Last Sold Summary

  • 38 Days On Market

  Last Listing Agent Megan Stanaford Black Diamond Realty

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